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Category:natural substances and extractives
US / EU / FDA / JECFA / FEMA / FLAVIS / Scholar / Patent Information:
Physical Properties:
| Assay: | 95.00 to 100.00
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| Food Chemicals Codex Listed: | No |
| Melting Point: | 76.00 °C. @ 760.00 mm Hg
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| Boiling Point: | 275.00 °C. @ 760.00 mm Hg
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| Vapor Pressure: | 0.005000 mmHg @ 25.00 °C. (est) |
| Flash Point: | 233.00 °F. TCC ( 111.50 °C. ) (est)
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| logP (o/w): | 3.380 |
| Soluble in: |
| | water, 38.39 mg/L @ 25 °C (est) |
Organoleptic Properties:
| Odor and/or flavor descriptions from others (if found). |
Cosmetic Information:
Suppliers:
| Alfa Biotechnology |
| For experimental / research use only. |
| Alantolactone 98%
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| BOC Sciences |
| For experimental / research use only. |
| Alantolactone ≥98%
Odor: characteristic Use: Alantolactone is sesquiterpene lactone, significantly reduces feeding and survival of Tribolium confusum.
Anti-inflammatory and antineoplastic |
| Coompo |
| For experimental / research use only. |
| Alantolactone from Plants ≥95%
Odor: characteristic Use: The sesquiterpene lactone, alantolactone, significantly reduces feeding and survival of Tribolium confusum. These findings support the view that alantolactone may protect plants such as composites from insect attack.
The phytotoxic action of alantolactone was evident by its inhibitory effects on seed germination, seedling growth, rate of respiration, and degradation of starch and proteins in mung beans (Phaseolus mungo L.). Some amino acids, bases of nucleic acids, and gibberellic acid partially alleviated the alantolactone-induced inhibition of the seed germination. |
| ExtraSynthese |
| For experimental / research use only. |
| Alantolactone (HPLC) ≥90%
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| Sigma-Aldrich: Sigma |
| For experimental / research use only. |
| Alantolactone ≥98% (HPLC)
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Safety Information:
| Preferred SDS: View |
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| Hazards identification |
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| Classification of the substance or mixture |
| GHS Classification in accordance with 29 CFR 1910 (OSHA HCS) |
| None found. |
| GHS Label elements, including precautionary statements |
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| Pictogram | |
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| Hazard statement(s) |
| None found. |
| Precautionary statement(s) |
| None found. |
| Oral/Parenteral Toxicity: |
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Not determined
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| Dermal Toxicity: |
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Not determined
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| Inhalation Toxicity: |
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Not determined
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Safety in Use Information:
| Category: | | natural substances and extractives |
| Recommendation for alantolactone usage levels up to: | | | not for fragrance use.
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| Recommendation for alantolactone flavor usage levels up to: |
| | not for flavor use.
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Safety References:
References:
| | (3aR,5S,8aR,9aR)-5,8a-dimethyl-3-methylidene-5,6,7,8,9,9a-hexahydro-3aH-benzo[f][1]benzofuran-2-one |
| NIST Chemistry WebBook: | Search Inchi |
| Pubchem (cid): | 72724 |
| Pubchem (sid): | 135029556 |
Other Information:
Potential Blenders and core components note
Potential Uses:
Occurrence (nature, food, other): note
Synonyms:
| | alant camphor | | (3aR,5S,8aR,9aR)-5,8a- | dimethyl-3-methylene-3,3a,6,7,8,8a,9,9a-octahydronaphtho[2,3-b]furan-2(5H)-one | | (3aR,5S,8aR,9aR)-5,8a- | dimethyl-3-methylene-3a,5,6,7,8,8a,9,9a-octahydro-3H-naphtho[2,3-b]furan-2-one | | 5,8a- | dimethyl-3-methylene-3a,5,6,7,8,8a,9,9a-octahydro-3H-naphtho[2,3-b]furan-2-one | | (3aR,5S,8aR,9aR)-5,8a- | dimethyl-3-methylene-3a,5,6,7,8,8a,9,9a-octahydronaphtho[2,3-b]furan-2(3H)-one | | (3aR,5S,8aR,9aR)-5,8a- | dimethyl-3-methylidene-3a,5,6,7,8,8a,9,9a-octahydronaphtho[2,3-b]furan-2(3H)-one | | (3aR,5S,8aR,9aR)-5,8a- | dimethyl-3-methylidene-5,6,7,8,9,9a-hexahydro-3aH-benzo[f][1]benzofuran-2-one | | | elecampane camphor | | | eupatal | | | helenin | | | helenine | | 8b- | hydroxy-4aH-eudesm-5-en-12-oic acid g-lactone | | | inula camphor | | | naphtho[2,3-b]furan-2(3H)-one, 3a,5,6,7,8,8a,9,9a-octahydro-5,8a-dimethyl-3-methylene-, (3aR,5S,8aR,9aR)- | | (3aR-(3aalpha,5beta,8abeta,9aalpha))-3a,5,6,7,8,8a,9,9a- | octahydro-5,8a-dimethyl-3-methylene naphtho(2,3-b)furan-2(3H)-one | | [3aR-(3aa,5b,8ab,9aa)]-3a,5,6,7,8,8a,9,9a- | octahydro-5,8a-dimethyl-3-methylenenaphtho[2,3-b]furan-2(3H)-one |
Articles:
| PubMed:UPLC/MS/MS method for quantification and cytotoxic activity of sesquiterpene lactones isolated from Saussurea lappa. |
| PubMed:Simultaneous Determination of Chlorogenic Acid, Caffeic Acid, Alantolactone and Isoalantolactone in Inula helenium by HPLC. |
| PubMed:[Inhibitory effect of alantolactone on the proliferation of K562/ADR cells and its mechanism]. |
| PubMed:Simultaneous determination of sesquiterpene lactones isoalantolactone and alantolactone isomers in rat plasma by liquid chromatography with tandem mass spectrometry: application to a pharmacokinetic study. |
| PubMed:Targeting apoptosis pathways in cancer with alantolactone and isoalantolactone. |
| PubMed:Alantolactone induces cell apoptosis partially through down-regulation of testes-specific protease 50 expression. |
| PubMed:Alantolactone induces apoptosis in RKO cells through the generation of reactive oxygen species and the mitochondrial pathway. |
| PubMed:Simultaneous Determination of Two Epimeric Furofuran Lignans (Sesamin and Asarinin) of Asarum heterotropoides Extract in Rat Plasma by LC/MS/MS: Application to Pharmacokinetic Study. |
| PubMed:Alantolactone induces apoptosis in chronic myelogenous leukemia sensitive or resistant to imatinib through NF-κB inhibition and Bcr/Abl protein deletion. |
| PubMed:Alantolactone induces apoptosis in HepG2 cells through GSH depletion, inhibition of STAT3 activation, and mitochondrial dysfunction. |
| PubMed:Alantolactone inhibits growth of K562/adriamycin cells by downregulating Bcr/Abl and P-glycoprotein expression. |
| PubMed:Conformational analysis of antistaphylococcal sesquiterpene lactones from Inula helenium essential oil. |
| PubMed:Alantolactone suppresses inducible nitric oxide synthase and cyclooxygenase-2 expression by down-regulating NF-κB, MAPK and AP-1 via the MyD88 signaling pathway in LPS-activated RAW 264.7 cells. |
| PubMed:Alantolactone induces apoptosis in glioblastoma cells via GSH depletion, ROS generation, and mitochondrial dysfunction. |
| PubMed:Alantolactone induces activation of apoptosis in human hepatoma cells. |
| PubMed:Mechanisms involved in enhancement of the expression and function of aggrecanases by hyaluronan oligosaccharides. |
| PubMed:Antistaphylococcal activity of Inula helenium L. root essential oil: eudesmane sesquiterpene lactones induce cell membrane damage. |
| PubMed:Alantolactone inhibits cell proliferation by interrupting the interaction between Cripto-1 and activin receptor type II A in activin signaling pathway. |
| PubMed:Screening for Compositae sensitization with pure allergens: implications of molecular structure, strength of reaction, and time of testing. |
| PubMed:Ultrasound-assisted extraction of alantolactone and isoalantolactone from Inula helenium roots. |
| PubMed:Structure-activity relationship studies on derivatives of eudesmanolides from Inula helenium as toxicants against Aedes aegypti larvae and adults. |
| PubMed:Activation of caspases and poly (ADP-ribose) polymerase cleavage to induce apoptosis in leukemia HL-60 cells by Inula racemosa. |
| PubMed:HPLC determination and NMR structural elucidation of sesquiterpene lactones in Inula helenium. |
| PubMed:Isoalantolactone from Inula helenium caused Nrf2-mediated induction of detoxifying enzymes. |
| PubMed:Microbial transformation of alantolactone by Mucor polymorphosporus. |
| PubMed:Separation and determination of alantolactone and isoalantolactone in traditional Chinese herbs by capillary electrophoresis. |
| PubMed:Nrf2-mediated induction of detoxifying enzymes by alantolactone present in Inula helenium. |
| PubMed:A rapid identification of Radix inulae and its active component alantolactone in the Tibetan medicine Manuxitang. |
| PubMed:Induction of detoxifying enzyme by sesquiterpenes present in Inula helenium. |
| PubMed:Simultaneous quantification of eudesmanolides and thymol derivatives from tissues of Inula helenium and I. royleana by reversed-phase high-performance liquid chromatography. |
| PubMed:Separation and determination of two sesquiterpene lactones in Radix inulae and Liuwei Anxian San by microemulsion electrokinetic chromatography. |
| PubMed:Erythema multiforme due to contact with weeds: a recurrence after patch testing. |
| PubMed:Antiproliferative sesquiterpene lactones from the roots of Inula helenium. |
| PubMed:Antifungal highly oxygenated guaianolides and other constituents from Ajania fruticulosa. |
| PubMed:Sensitization and cross-reaction patterns in Danish Compositae-allergic patients. |
| PubMed:Cytotoxic sesquiterpene lactones mediate their death-inducing effect in leukemia T cells by triggering apoptosis. |
| PubMed:Patch test sensitization to Compositae mix, sesquiterpene-lactone mix, Compositae extracts, laurel leaf, Chlorophorin, Mansonone A, and dimethoxydalbergione. |
| PubMed:Cytotoxic Michael-type amine adducts of alpha-methylene lactones alantolactone and isoalantolactone. |
| PubMed:Antimycobacterial eudesmanolides from Inula helenium and Rudbeckia subtomentosa. |
| PubMed:Allergic contact dermatitis associated with photosensitivity, from alantolactone in a chrysanthemum farmer. |
| PubMed:Patch testing for Compositae allergy. |
| PubMed:In vitro model for contact sensitization: I. Stimulatory capacities of human blood-derived dendritic cells and their phenotypical alterations in the presence of contact sensitizers. |
| PubMed:Erythema-multiforme-like eruption following allergic contact dermatitis from sesquiterpene lactones in herbal medicine. |
| PubMed:Airborne contact dermatitis from Frullania. |
| PubMed:Sesquiterpene lactone contact sensitivity: clinical patterns of Compositae dermatitis and relationship to chronic actinic dermatitis. |
| PubMed:A murine in vitro model of allergic contact dermatitis to sesquiterpene alpha-methylene-gamma-butyrolactones. |
| PubMed:A successful murine model for contact sensitization to a sesquiterpene-alpha-methylene-gamma-butyrolactone: sensitization to alantolactone in four strains of mice. |
| PubMed:Treatment of dermatitis caused by the sesquiterpene lactone helenin. |
| PubMed:Cross-reaction in allergic contact dermatitis from alpha-methylene-gamma-butyrolactones: importance of the cis or trans ring junction. |
| PubMed:In vitro inhibition of mouse hepatic mixed-function oxidase enzymes by helenalin and alantolactone. |
| PubMed:Contact dermatitis to sesquiterpene lactones in Inula viscosa Aiton. |
| PubMed:[Helenine and santonine, the 12-carboxy-eudesma-3,11(13) diene]. |
| PubMed:[Contact eczema caused by Chrysanthemum morifolium Ramat]. |
| PubMed:Contact dermatitis to Alstroemeria. |
| PubMed:[Gaillardia allergy]. |
| PubMed:Contact dermatitis from Frullania, Compositae and other plants. |
| PubMed:Helenin inhibition of liver microsomal enzymes. |
| PubMed:Allergic contact dermatitis to methylenelactones. Use of lymphocyte transformation test. |
| PubMed:The sensitizing capacity of helenin and of two of its main constituents, the sesquiterpene lactones alantolactone and isoalantolactone: a comparison of epicutaneous and intradermal sensitizing methods in different strains of guinea pig. |
| PubMed:Synthesis of alpha-methylene-gamma-butyrolactones: a structure-activity relationship study of their allergenic power. |
| PubMed:Allergic contact dermatitis to alpha-methylene-gamma-butyrolactones. Preparation of alantolactone-protein conjugates and induction of contact sensitivity in the guinea pig by an alantolactone-skin protein conjugate. |
| PubMed:Photosensitivity and allergy to aromatic lichen acids, Compositae oleoresins and other plant substances. |
| PubMed:Photosensitivity and allergy to aromatic lichen acids, Compositae oleoresins and other plant substances. |
| PubMed:Studies on a strain of Fusarium solani (Mart.) Sacc. Isolated from a case of mycotic keratitis. |
| PubMed:Alantolactone in chrysanthemum extract. |
| PubMed:Allergic contact dermatitis due to sesquiterpene lactones. A comparative study of human and animal sensitivity to alpha-methylene-gamma-butyrolactone and derivatives. |
| PubMed:Alantolactone sensitivity in chrysanthemum contact dermatitis. |
| PubMed:Synthesis of and allergic contact dermatitis to bicyclo-[2,2,1]-heptyl-alpha-methylene-gamma-butyrolactones derived from norbornene and camphene. |
| PubMed:Toxic effect of alantolactone and dihydroalantolactone in in vitro cultures of leukocytes. |
| PubMed:Compositae sensitivity among patients with contact dermatitis: value of compositae oleoresins in a standard test series. |
| PubMed:Contact hypersensitivity to sesquiterpene lactones in Chyrsanthemum dermatitis. |
| PubMed:Chrysanthemum allergy. Pt. II: Experimental studies on the causative agents. |
| PubMed:Reaction of alantolactone, an allergenic sesquiterpene lactone, with some amino acids. Resultant loss of immunologic reactivity. |
| PubMed:The structure of alantolactone. III. Configurations of 4-methyl group in tetrahydroalantolactone and several 3-hydroxytetrahydroalantolactones. |
| PubMed:The structure of alantolactone. II. The conversion of alantolactone into dihydroeudesmol. |
| PubMed:The conversion of alantolactone into dihydroeudesmol. |
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3D/inchi